Pyridine → HCID 86652271、化合物

HRID 1256294ノート

反応式

HRID 1256294 の反応式
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:12])[CH:3]=1.N1C=CC=CC=1.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:23][CH:24]=2)[CH:3]=1

参加物

4

反応物 3

HCID 1049PyridineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amine

生成物 1

HCID 86652271HCID 86652271、化合物収率 51.3%

反応条件

温度
0 °C

実験手順

To a 20 mL scintillation vial was added 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1.1, 0.207 g, 1.131 mmol) and pyridine (2.84 ml, 35.1 mmol) and the solution was cooled to 0° C. To the yellow solution was added 4-(trifluoromethoxy)benzoyl chloride (0.508 g, 2.262 mmol) to give an orange suspension. The reaction mixture was stirred for one hour, quenched by the addition of saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure in the presence of silica gel. The silica-adsorbed material was then purified by silica gel chromatography (25-75% ethyl acetate/hexanes gradient) to afford the desired compound N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide 14A as an orange solid (215 mg, 51% yield); ESI-MS: m/z 370.0 (M+H)+.

後処理

  1. customto give an orange suspension
  2. customquenched by the addition of saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure in the presence of silica gel
  7. customThe silica-adsorbed material was then purified by silica gel chromatography (25-75% ethyl acetate/hexanes gradient)

出典と根拠

ORDレコード
ord-05b2e17cd2974551b7be0fe01a73a898
出典データセット
uspto-grants-2013_06
特許番号
US08461163B2

反応ノート

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